I am a Canadian male, mid 40s, have 6 years in Latin America, primarily Mexico. Teaching Certificate, a lot of Business English experience. Also construction technical background with 3 trade certs. I plan future online studies to complete a degree. I would appreciate any objective tips. I suppose I'd need to enter on a tourist visa.

I will be happy to exchange info on Mexico; can even supply leads on work. I am free-lance here.

I lived in Leon for a few years as a business person but never taught English there. What is the pay and the standard of living?
In Taiwan it is best to find block hours, that pay by the hour. A degree is not necessary, just don't tell people you don't have one.
The average pay is 500 to 700nt per hour. Salary positions usually pay considerably lower.
Work permits are required to work but the laws and regulations are seldom enforced. If you do not have a university degree, it will be very difficult for you to obtain a legal working permit. You may still be able to get one, but not in Taipei. There are several very disreputable placement agencies in Taichung and Koashiung, that can get you a work permit, but they will pay you little or nothing.
I would recommend you get a a multiple entry, tourist visa for business purposes, i.e. product procurement, with a letter of introduction from a local company. That should get you a long duration, multiple entry visa. This visa can be changed for work or study purposes, if you choose. Should you choose to work under your tourist visa, you will have to make visa runs every two months or sign up for classes. Visa run cost will be comparable to tax withholdings under a work permit. Be advised it is illegal to obtain employment in this manner but again, labor laws in Taiwan are seldom enforced.
Once in Taiwan begin looking for work, don't agree to anything before you get here as offers given outside Taiwan are bottom of the barrel. Please understand that it is the local custom to "exaggerate pay and benefits, while forgetting to mention additional work requirements, so ask a lot of questions and try not to sign anything before working for a while.
Good luck,
EOD